Hydrochloric Acid → HCID 135774107, compound

HRID 720108Notes

Reaction equation

HRID 720108 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:20](=[O:21])[NH:19][N:18]=[CH:17][C:6]3=[C:7]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[NH:8][C:9]([CH:10]=1)=[C:5]23.[CH2:22]([N:24]([CH2:27]C)[CH2:25][CH3:26])C.F[P-](F)(F)(F)(F)F.N1([O:45][C:46](N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.Cl.[CH2:54](Cl)Cl>CN(C)C=O.CO>[CH3:27][N:24]([CH3:22])[CH2:25][CH2:26][CH2:54][C:46]([NH:1][C:2]1[CH:3]=[C:4]2[C:20](=[O:21])[NH:19][N:18]=[CH:17][C:6]3=[C:7]([C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=4)[NH:8][C:9]([CH:10]=1)=[C:5]23)=[O:45]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6344Dichloromethane2×HCID 8471Triethylamine2×HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 1357740798-Amino-2-phenyl-1,5-dihydro-[1,2]diazepino[4,5,6-cd]indol-6-one

Product 1

HCID 135774107HCID 135774107, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Preparation of example 57 from the title compound of Example 7 (hydrochloride) (27 mg, 0.086 mmol), 4-dimethylamino-butyric acid(hydrochloride)(17 mg, 0.104 mmol), triethylamine (0.036 mL, 0.258 mmol), and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (40 mg, 0.104 mmol) in CH2Cl2 (0.3 mL) and N,N-dimethylformamide (0.3 mL) was carried out analogously to Example 11. Silica gel chromatography (2% triethylamine in 9:1 CH2Cl2:methanol) of the freebase afforded, after acidification with HCl, the title compound (18 mg, 0.042 mmol) as a yellow powder in 49% yield.

Sources & evidence

ORD record
ord-83ab5a50a1ac4bf48754c8effd1638e7
Source dataset
uspto-grants-2006_11
Patent number
US07132533B2

Reaction notes

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